Let me tell you about a couple of cases I lost. Now, wait: before the Commentariat sharpens its knives (“This guy couldn’t get a big-firm job, then loses all his cases. No wonder he’s writing for ATL. Heh.” — Guest), let me point out a few things. In 17 years as an employment litigator, I’ve won plenty more cases than I’ve lost. But I didn’t learn as much from the cases I won; I learned much more from the ones I lost.

So this post covers the single most important lesson I’ve learned in litigation, and now I’m sharing it with you. You didn’t learn it in law school, and you’re not likely to find a CLE on it. But the lesson these two cases illustrate can prevent you from making the most common mistake lawyers make.

And learning that lesson will help you win more cases.…

When I was a fourth-year associate in a five-lawyer shop, I had the unusual opportunity to argue a case at the First Circuit. I’m not sure that I realized just how unusual it was at the time; employment lawyers don’t tend to do a lot of appellate work, and I haven’t been back since.

The situation was also unusual. We had won a sexual-harassment jury trial, successfully defending a car dealership in federal court. But the insurer balked at paying our bills, arguing that our partial-summary-judgment win on the negligence claim ended its duty to defend before the trial took place. The dealership wanted us to go after the insurer, even if it was a fool’s errand, and the partner in my firm was happy to let a fool like me (and another associate) run with it.

When we were researching the case, we discovered an arcane holding in Massachusetts law that essentially said that an insurer couldn’t just opt out of a case once it was in; it had to be let out by the court. We argued this point in the district court and lost at summary judgment. The car dealer wanted to appeal, so we did. We knew that we had the law on our side, even if it was a technicality. It was The Law.

I’m not going to lie to you. My first (and last) First Circuit argument was not a thing of beauty. I stumbled out of the gate, telling the three-judge panel what was painfully obvious — that it was my first time there. My colleague still refers to it as my “sports-radio opening” (“Uh, hi guys, long-time listener, first-time caller.”). But I rallied, wrapping myself in the flag of the rock-solid case law that said, essentially, we win.

But the presiding judge wasn’t buying what I was selling. “But isn’t it true, Mr. Shepherd, that the insurer only got in because of the negligence claim?”

“Yes, Your Honor.”

“And then you won summary judgment on the negligence claim.”

“Yes, Your Honor.”

“So without the negligence claim, shouldn’t the insurer be off the hook?”

“No, Your Honor. The law says ….” But he didn’t care so much about the law, because the facts went the other way. Judgment affirmed. We lost.

Fast-forward a dozen years. By then I’m an experienced litigator, and a specialist in noncompete cases. The would-be founders of a startup company come to us for help getting out of their noncompetes. We told them what to do and not do: most importantly, don’t take any secret documents when they leave their employer. Perhaps they misheard me, because they took every secret document. (Awesome.)

The thing is, I had several fantastic legal arguments to show that their noncompetes were unenforceable. The noncompetes were basically written by someone pounding the keyboard with his face. (Free shot, commenters: “Yeah, Shepherd’s pounding the keyboard with his face. Heh.” — Guest.) Legally, I could not lose. The law basically said we win.

But that’s not how it works in court. While we did keep the judge from shutting down the startup, she issued an injunction that made it very difficult for them to get off the ground. And how much substantive law did the judge cite in her five-page decision? Zero. Because the law didn’t matter.

The facts did.

In this case, the facts were that my clients did something they shouldn’t have done, and the court punished them for that. My completely correct, rock-solid legal arguments didn’t matter.

Same with the First Circuit case. The facts were that the insurer only had to defend the case because there was a negligence claim, which we knocked out before trial. My completely correct, rock-solid legal arguments didn’t matter.

And in both cases, based on the facts, they were the “right” decisions. Just not based on the law.

In law school, we learn all about the law. They don’t call it “fact school.” We learn about the law and we think we’re fancy and we show off how we can cite to cases and statutes, repelling the normal humans around us. Then as lawyers, we spend our time researching cases and statutes, and we craft our clever legal arguments, and we fall in love with them. Because facts are just stories, and anyone can tell stories. My Uncle Pete can tell stories. But he can’t cite cases or statutes. (I don’t have an Uncle Pete. It’s kind of a parable. Work with me here.) Knowing the law makes us special.

But it’s the stories that win cases. The facts.

I’ve made it a point to ask judges about this when I meet them outside of court. Every single one I’ve ever asked has agreed: Facts win cases.

What does this have to do with small firms? Well, here’s where we have an advantage. In large firms, you’re more likely to do research memos, which focus on the law. Oftentimes, junior associates are told to research issues without knowing the specific facts of the case. In smaller firms, we don’t usually do memos. So we’re less likely to get hung up on the law. And all the lawyers, even the most junior ones, are intimately involved with the facts of the case.

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